


pretty.

by ruzekhalstead



Series: halstead & upton mini-fics. [1]
Category: Chicago Fire, Chicago Med, Chicago PD (TV)
Genre: Chicago Fire - Freeform, Chicago Med - Freeform, Chicago PD - Freeform, Drunk Hailey, F/M, Jealous Jay, Molly's (Chicago Fire), One Chicago (Chicago Franchise), Upstead
Language: English
Status: Completed
Published: 2020-04-01
Updated: 2020-04-16
Packaged: 2021-02-28 16:54:35
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,673
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23420515
Author URL: https://archiveofourown.org/users/ruzekhalstead/pseuds/ruzekhalstead
Summary: “alright, so answer me this. hypothetically, if hailey was to go home with, oh, i don’t know, severide or something, would you be completely okay with that?”“i would – i would be fine."-prompt: the whole gang is at molly's having a great time until will halstead corners jay about his relationship with hailey and advises him to take his girl home. (un)fortunately, hailey isn't interested in going back to her home.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead & Will Halstead, Jay Halstead/Hailey Upton
Series: halstead & upton mini-fics. [1]
Series URL: https://archiveofourown.org/series/1914352
Comments: 15
Kudos: 133





	1. chapter one

hailey never drinks this much. seriously. ever.

somehow, she gets caught up with the crowd at molly's and the shots start flowing. it doesn’t help that her drinking partners include kelly severide, adam ruzek and joe cruz, among the rest of the first responders that tag along.

she had made her way over with her own squad and mingled with the rest of their friends. currently she has her arm wrapped around severide’s waist, with his around her shoulders and they are screaming the lyrics to whatever song is currently playing. adam is grabbing everyone another round of tequila shots while kim is serenading hailey from across the booth. the rest of the first responder ladies are present too; vanessa, sylvie, emily, natalie and april sitting at their own booth enjoying the night. the majority of the guys are settled at the bar; jay, will, matt and kevin conversing over beers.

jay trusts hailey wholeheartedly and there’s no question about it. however, he can’t help but worry, considering he’s never seen her consume so much alcohol in such little time. especially because she has kept up with every single drink severide has had and he’s seen severide quite drunk before.

“jay, if you’re going to keep looking at her every five seconds, you may as well just go over there now,” will whispers, raising an eyebrow at his brother. he lowers his voice so the rest of his friends don’t hear (but honestly, will is convinced literally everyone but them knows those two are in love with each other).

jay instantly turns his attention to his brother, his cheeks pinking at getting caught. “i'm just keeping an eye,” he replies, sipping his beer.

“yeah, clearly,” will rolls his eyes. “so, are you two dating yet?”

jay sputters, easily choking on his drink. “what the hell are you talking about, man?”

will lifts an eyebrow at jay's immediate denial. “i mean, i have eyes, jay,” he explains, as if it’s obvious. “dude, you’re obviously in love with her.”

“have you been helping yourself to the hospital’s medicine cabinet?”

will furrows his brows. “are you asking if i’m on drugs?” jay looks at him expectantly. “you're clearly not very perceptive.”

“i do just fine, thanks,” jay rolls his eyes as he finishes the last of his beer. “hailey and i are just partners, that’s all, and you know that.”

“bullshit,” will says with a single smirk.

jay levels him with an incredulous stare; his brother can be such a pain in the ass sometimes. “we're partners, will; we see a lot of hard shit every day and we’re close. But that’s all it is.”

“alright, so answer me this,” will replies and jay rolls his eyes, literally debating just walking out right now. “just humour me,” he cuts him off. “hypothetically, if hailey was to go home with, oh, i don’t know, severide or something, would you be completely okay with that?”

instinctively, jay looks over at hailey again. she's still nestled close to severide, but it didn’t bother him until now.

“i would – i would be fine,” jay replies but flinches when he stumbles on his words. this is exactly what will is waiting for, like a vulture.

he finishes off his beer with a smirk, “my point is proven, and i'm finished here.”

jay's jaw clenches tight. he's annoyed with his brother and now he can’t stop looking at severide’s arm around hailey without wanting to rip it off.

will halstead, everyone.

“i'm heading home,” will digs into his pocket to drop some bills on the counter, winking at herrmann. “you should probably take your girl home though, make sure she gets into bed safely. you know, her own bed.”

jay glares at him. “you’re a dick and i hate you so much right now.”

“goodnight bro,” will laughs, completely unaffected by his younger brother’s words. he pats him on the shoulder and says, “love you.”

regardless of how annoying his brother is and how he knows exactly how to push his buttons, will is basically the only family he has left. which is why he replies with a quiet “love you too” before ordering a whiskey to counteract his brother’s words.

it feels as if it’s karaoke night at molly’s with the amount of singing currently taking place. it’s loud and terribly off-key but they’re all having a great time and he can’t help but chuckle when he hears adam attempt celine dion’s m _y heart will go on._

jay finds himself by himself at the bar, staring at his half empty glass. matt and kevin have gone to join the ladies in their booth, but jay doesn’t want to join them. if he’s being completely honest, the only person he wants to talk to is hailey, but she’s otherwise occupied. he's debating whether or not he should make his way home, when he feels a weight tumble into his side.

he nearly falls off his stool but catches himself with a foot on the floor and a hand on the bar.

“oops,” hailey giggles and jay looks over to see her clutching onto the bar for dear life.

it's odd to see her so clumsy and giggly since she is always so cool and collected. she very rarely lets down her walls, much like himself. and when she does, it’s because something big has prompted it and she needs to vent.

“you alright?” he raises an eyebrow as she attempts to hop onto the stool beside him. he opts to grabbing her arm and guiding her to ease the difficulties she’s having; she’s still giggling. “can we get a water please?” jay asks herrmann behind the bar and the firefighter sends him a smirk but obliges anyway.

hailey finally settles in her seat and swivels to face jay. her eyes are glazed over and she’s smiling goofily; honestly, it’s a sight he thought he’d never see. “i saw you all alone and thought you needed some company.”

“actually, i’m thinking of heading out soon,” he replies as he pushes the glass of iced water in her direction. she wrinkles her nose as it, but he pushes it further with a stern look.

hailey gives in and takes two large gulps. “i should too. i'm getting very sleepy,” she adds, her eyes dropping for dramatic effect.

or so jay thinks it’s for dramatic effect but then he genuinely thinks she’s sleeping at the bar. “hailey, wake up,” he chides, chuckling because he can’t help himself; she looks adorable. “come on, drink your water.”

hailey blindly reaches for the glass again but refuses to open her eyes. once again, he’s not surprised she doesn’t listen to his instructions. her arms rest against the bar and she moves to drop her head against it too. “alright,” he laughs, “do you want me to take you home?”

her eyes instantly pop back open and her blue eyes stare at him in adoration. “take me home, jay halstead.”

jay swallows roughly but drops a few bills on the counter and bids goodnight to herrmann.

hailey is up and out of her seat within seconds and a newfound source of energy. she bounds over to her group from earlier, yelling cheerful goodbyes as she runs into kim for a messy hug. jay follows her, standing behind and waiting for her like a dutiful partner (or so he convinces himself). she shares a hug with adam and jay tenses when she moves to say goodbye to severide (honestly, he was so dramatic).

but all hailey does is steal his shot glass and drain it, while severide laughs and ruffles her hair. and suddenly, jay feels like an idiot for the jealous thoughts that consumed him earlier because clearly, their relationship is barely anything more than sibling-like. with that, jay says a quick goodbye to his co-workers and friends and walks hailey out the door.

he tries, he really does. but as soon as he opens the door so she can exit ahead of him, he realizes she can hardly even walk, much less in a straight line. hailey's giggling as she stumbles into the brick wall, so jay gently grabs her arm to guide her in the direction of his truck. hailey takes full advantage of the closeness and snuggles up as close as she can.

“you’re going to have a hell of a hangover tomorrow,” jay murmurs quietly. he's opening the passenger door and helping her up into the vehicle. her foot slips on the outside step and jay hastily grabs her before she falls on the ground.

she's still laughing, and he hoists her into the truck and fastens her seatbelt; he isn’t taking any more chances. “impossible. i'm greek, we don’t get hangovers,” she replies as he’s stretched over her. he can smell the tequila on her breath and accidentally catches her gaze as he pulls back. her blue eyes are mesmerizing and they’re staring at him with such intensity, he forgets his purpose for a moment.

“somehow i don’t think that will be the case tomorrow,” he says quickly to distract himself from her captivating gaze. he closes the door and makes his way to the driver’s side and does everything he can to avoid looking at her. she doesn’t make it easy; she’s purposely staring right at his side profile.

his jaw is twitching; he knows it, but he can’t control it. “where are we going?” she asks suddenly.

“i'm dropping you off at your place?” jay answers in a questioning tone.

hailey instantly protests, her arms crossing and her lips pouting. “i don’t want to go home,” she says defiantly.

“hailey, you have to go home. we have to work in the morning, and you need to sleep off that hangover,” jay's voice is gentle, but hailey is not having it.

clearly, she isn’t getting more sober as time goes on and jay sighs. “jay, do not take me home – i don’t want to go.”

he humours her. “where do you expect me to take you then? it's one in the morning.”

a slow smile spreads across her features. “i want to go to your place.”

jay sputters for a moment but regains his composure quickly. “what? my apartment?”

“yeah,” she’s still giggling. “you have that really good scotch and i could really go for a glass right now.”

jay shakes his head but can’t help the amused smile; she’s been drinking tequila all night but now wants to switch and mix whiskey. he doesn’t think farther into it, doesn’t want to let his mind get distracted with hypotheticals. instead, he makes the rest of the short trip to his apartment and holds his hobbling partner all the way to his door.

she's an obliterated giggling mess and he doesn’t even find himself growing irritated.

hailey’s smart and she heads straight for the scotch, but he knows better. “not a chance in hell,” he quips as he swipes the bottle before she gets her hands on it. he holds it above his head where she definitely can’t reach and then places it on an even higher shelf.

“jay,” she whines with a frown and sways on her feet.

jay places a hand on her waist and shuffles her in the direction of his bedroom. “come on hailey, let’s get some sleep,” he’s practically begging. “we have to be up so early.”

upon hearing the pleading in his voice, hailey concedes and allows him to push her in the direction of his bedroom. she’s been in it before but never to spend the night. she’s honestly too drunk to think anything more of it. when she spots his bed, she dives face first and ignores his snickers.

jay is rummaging through his drawers and pulls out an old police academy long-sleeve (his biceps were much smaller at the time) and a pair of sweatpants for her to change into. when he turns around, she is already sitting up and waiting for him expectantly, so he throws the clothes at her face. her reflexes are understandably inebriated, just like the rest of her.

she’s laughing again. “thanks halstead!”

by the time he turns back to face her, her t-shirt is up over her head. they're both adults and professionals, so he doesn’t hastily turn away as if his eyes are burning. he’s mature and raises a single eyebrow in her direction.

hailey's smirking. “sorry,” she says but she’s the least bit apologetic. she’s attempting to take off her jeans now, but they get stuck around her ankles and her vision is swimming too much for her to focus. “jay,” she murmurs, “help.”

“this would probably be easier if you took off your shoes,” he replies as he unties her boots and sets them by his door. she saves him the embarrassment and tugs off the rest of her jeans. she takes the shirt he threw at her and pulls it over her head, reveling in the warmth. she loves how it smells like fabric softener but still smells like jay.

hailey takes one look at jay’s old sweatpants and throws them back at him. “i don’t wear pants to bed,” she wrinkles her nose in distaste 

jay mumbles something under his breath but folds and places the pair of sweats back into their rightful drawer. he's trying so hard to keep his shit together, but she is not making it easy. hailey wastes no more time and pulls back the covers to get comfortable underneath them. she pulls them up below her neck and watches jay as he moves about his room, with the brightest blue eyes. there’s something about seeing her like that, in his bed, so carefree, that he just can’t look at her without melting.

jay grabs an extra blanket from his closet and heads for the door. “i’ll bring you some water and advil before i turn in. but you should get some sleep, i'll wake you up in the morning.”

hailey’s eyes grow confused and her limbs stretch out from underneath the blankets to reach for him. “no, jay, where are you going?”

she’s clearly getting sleepy once again. “i'm sleeping on the couch tonight. i'll see you in the morning.”

he tries to leave again but hailey sputters and nearly rolls off the bed trying to stop him. he sighs and rushes forward to steady her. “jay, please don’t sleep on the couch,” hailey says quietly. her eyes are fluttering sleepily, and jay knows it’s only a matter of time before she’s out like a light. “i want you to sleep here.”

jay stares at her by can’t quite get a read on her. “okay,” he replies, just as quietly, “just let me go get—”

“no!” she clutches onto his arm. “just come to bed.”

jay plans on protesting again, because she’s drunk and she may not feel this way in the morning, but all his self-control is gone. “okay,” he agrees.

she lets go of his arm with a satisfied smile and she looks adorable. jay is quick to shed his clothing, losing his shirt and changing into sweats. he debates whether or not he should put on a clean shirt, because he wants hailey to be comfortable but finds it super uncomfortable for him. he reaches for one anyway, but hailey is quick to object. “no shirt,” she says, and he raises an eyebrow, “i know you don’t like to sleep with shirts.”

he concedes and finds himself crawling into his side of the bed after turning off the light. hailey is quick to gravitate towards him (she’s been waiting for him to get into bed for ages, or so it feels like it). she drapes an arm across his chest and tangles her bare legs with his and she snuggles her head close to his neck. the closeness is nice, and he exhales as he wraps an arm around her frame.

“this is nice,” hailey mumbles quietly, but jay hears her loud and clear from her positions close to his ear. “you have the perfect body to cuddle.”

jay can’t help but laugh. “uh, thank you?”

“really muscular,” her cold hands start roaming his upper chest and he tries not to go rigid.

instead, he chuckles nervously. “alright hailey, you’re drunk. it’s time to get some sleep.”

“yeah, i'm drunk,” she admits quietly, “but i think you’re really pretty and i should tell you that more often.”

jay is still laughing but the exhaustion is slowly starting to hit him. “thanks hails, i think you’re pretty too.”

“yeah, i know,” she mumbles, “i can see it in the way you look at me.”

jay should probably be surprised or caught off-guard or something. but he isn’t.

instead, he feels her lips press against his neck before he dozes off.


	2. chapter two.

**Notes for the Chapter:**

> PART TWOOOOOOO AS REQUESTED
> 
> actually took me a while to write and im sorry if the ending sucks I HAD SO MUCH TROUBLE WITH IT
> 
> im also working on an upstead+erin thing so look out for that!!
> 
> anyway enjoy & don't forget to comment!!
> 
> also be sure to follow me on tumblr; ruzek-halstead!!

the following morning, hailey awakes to a thundering pain in her skull.

it’s unfamiliar to her, considering she can count the number of hangovers she’s ever gotten on one hand, but she recognizes it clearly. she groans and digs her face deeper into the pillow. her mouth is dry, and she can hardly hear her own thoughts through the pounding happening in her head.

and to top it all off, she knows she has to work this morning.

her arm reaches out to her right side, blindly searching for her phone. instead, her fist comes in contact with something solid and she freezes.

hailey always sleeps on the left side of her bed. she always leaves her phone charging on the right side of her bed; the closer it is to her, the better she’ll hear it when it goes off in the middle of the night. her phone isn’t there, but apparently something else is.

she hears a low moan after she freezes and her head pops up off the pillow quickly to see jay, his eyes closed in pain (and exhaustion). he's lying on his side, shirtless and the bed covers are riding extremely low. hailey can feel herself paling (as if she wasn’t already before because she’s definitely hungover as hell). her wide eyes dart around the room to notice she isn’t in her bedroom at all and one quick look downwards, she realizes she isn’t wearing any of her clothes… or pants.

“oh my god,” she mumbles and watches as jay’s eyes fly open.

to her horror, a slow grin spreads across his facial features. “oh, you’re awake,” he says nonchalantly, rubbing the sleep from his eyes. “how are you feeling?”

hailey is still unable to speak; she continues to stare at him.

jay furrows his eyebrows. “we had a pretty crazy night. can you remember anything?”

of course, she couldn’t. and just trying to remember makes her head feel like it’s going to pop right off.

“jay, what the hell happened last night?”

her voice surprises her; it’s hoarse and groggy and her throat feels like she smoked a dozen cigarettes last night.

the sun outside shifts and the rays blind her through his window; she hastily tries to cover her eyes, but the exertion is literal pain.

“you don’t remember anything?” she takes a peek at his expression after hearing the humour in his voice. jay is smirking and she wants to strangle him.

“no, jay, i can’t remember anything,” she snaps. “i feel like i consumed all of molly’s liquor last night and i think i'm dying because everything hurts. and now i’m waking up in your bed with no pants on, so tell me, what the hell happened?”

jay has the audacity to start laughing.

“i don’t know if i should say anything. watching you panic is pretty cute,” he replies, lifting himself off of the bed. hailey is slightly relieved to see that he is wearing pants, but that does little to ease her nerves. but then she gets distracted looking at his sculpted chest and abdominal muscles and that only fuels his amusement further. he’s smirking because he’s remembering her comments about his muscular body the night before.

hailey shoots him a venomous glare and whips back the covers, praising the gods that the shirt she’s wearing is long enough to keep her decency intact. “i'll show you cute when i kick your damn ass, jay halstead,” she sasses as she also gets out of bed.

she's hit with an instant wave of nausea and she knows its game over.

she doesn’t get a chance to listen to his smartass comments or give another one of her own before she’s storming past him and into his bathroom. she kicks the door shut behind her but doesn’t get the opportunity to lock it. god knows he’s seen her in worse conditions, but this felt much too personal. as she’s busy spilling her stomach contents, she feels him come up behind her and gather her messy blonde locks behind her and out of her face. she can feel him rubbing her back gently and she’s so angry that he let her drink as much as she did.

her sickness finally ends, and she slumps against the cool tile floor.

“you were saying?” jay quips and she doesn’t have the energy to punch him in the face. “something about kicking my ass?”

she hears him snicker and leave the room, but she can’t find it in herself to move. a minute later, jay crouches down in her line of vision with a cold glass of water and two advil tablets. he raises an eyebrow when she doesn’t move and so she eventually sits back up to take the medication and hydrate.

“how in the world did i drink that much?” she asks desperately, grabbing onto his bicep to help her up. “and why the hell do you look so good?”

jay reaches under the sink cabinet and pulls out a toothbrush still in its package. “well, you and severide were hitting it pretty hard.”

hailey groans, “severide,” she moans.

“you guys were pretty cozy too,” he adds offhandedly. he tries to look nonchalant, but hailey can see right through him.

she raises an eyebrow. “not sure what your tone is implying jay, but severide is taken.”

jay rolls his eyes. “yeah, i know that,” he replies softly. he hands her the toothbrush and makes his way back into his bedroom.

hailey quickly rips open the package and brushes her teeth; she’s definitely going to need some more information on what just happened. when she makes her way back into jay's room, he’s rummaging through his drawers for a clean shirt, already dressed in his jeans. she sits on his bed and stares unabashedly.

“what?” he says self-consciously when he turns to face her.

her brain still hurts and she’s starting to think it’s because she’s remembering the night before. “did i call you muscular yesterday?” she asks, cringing.

a smirk appears on jay's face. “why yes, you did. thank you; i appreciated all the compliments from yesterday.”

hailey groans loudly. “what else did i say?”

“you also called me pretty, but i already knew that.”

“you're an ass, jay halstead.”

she silently watches as he puts on a clean shirt.

“i told you you’re pretty too,” he says, suddenly flustered.

she finds his nervousness adorable. “well, i already knew that.”

he rolls his eyes but there’s still tension in his shoulders. “come on; we can pass your place so you can change.”

hailey nods, even though her limbs are screaming at her to not be moved for the next seventy-two hours. she grabs her jeans from the night before and quickly puts them back on. jay is waiting by the door; phone, wallet and keys in his hands, along with hailey's purse from last night.

she sends him an appreciative look before taking it and making her way outside. their drive is quick and quiet and as Jay drops her off, he promises to be right back and ignores her questioning protests.

hailey takes the quickest ten-minute shower possible and changes into a new pair of black jeans. she's about to change into a new shirt but as she’s looking into her mirror, decides she actually looks really good in jay's shirt. it's long-sleeve and black and she tucks the front into her jeans, rolls up her sleeves and she’s ready for action. she shoves her phone into her back pocket and grabs her olive-green bomber jacket and heads for the door.

true to his word, jay is patiently waiting for her to get ready. as she gets into the passenger seat, she’s delighted to see he’s holding a steaming cup of hot coffee out for her. she smiles and her eyes roll back into her skull because it tastes so good.

hailey casts a look towards jay and catches his smirk. “what’s that look for?” she asks, lightly hitting his shoulder.

“i'm just noticing you didn’t change your shirt,” he replies, but he can’t drop the smirk.

hailey rolls her eyes. “i was lazy and rushing. also, this outfit looks really good,” she defends herself. “and if you’re going to say that this shirt looks better on me, please remember i have a gun and absolutely hate clichés.”

“are you kidding me?” jay raises an eyebrow. “i look way better in that shirt than you do.”

hailey smiles, satisfied with his answer.

as they pull into the district, he pauses before he exits the truck.

“there is one thing i do want to mention,” he says, hesitating slightly. hailey furrows her brows but waits for him silently. “i don’t know if i should be saying anything at all. but will got in my head and now i can’t stop thinking about it,” his hand is running through his hair and she hasn’t seen him this distressed in a long time.

hailey is more confused than ever.

“i was jealous last night,” jay blurts out. he turns to look at her and continues, “i saw you with severide and i never thought anything of it. and then will threw me a hypothetical if you were to go home with him and i kind of lost it.”

it's a lot of information to take in at once.

“will said what?”

jay brushes it off. “anyway, it got me thinking. and then last night—”

“what about last night?” hailey raises a curious eyebrow.

“you said you could see it in the way i looked at you,” he replies softly. they're still in his truck and he’s avoiding meeting her eyes, but hailey is turned in his direction, fully invested in his words. “it got me thinking. maybe i…”

hailey has literally never heard him express his feelings like this before. especially about her.

“maybe you what?” she urges, eyes wide.

he finally glances at her and breaks into a nervous chuckle. “maybe there’s something here that i'm overlooking?”

“between us?” hailey questions innocently.

god she’s so hungover.

“i'm really bad at this,” he groans, turning away again.

“no, jay,” hailey protests, grabbing onto an arm to pull him back towards her. “please, finish.”

he focuses his green eyes on his grinning partner. “i was jealous, and i honestly have no reason to be.”

“jay,” she laughs. “what are you trying to say?”

jay groans because he seriously sucks at this. “i like you, okay? and i don’t know exactly what that means, but i know i don’t ever want to see you with some other guy and have to wonder if you’ll be leaving with him.”

hailey sends him a small smile. “you don’t have to worry about that,” at jay's questioning look, she continues, “the only person i want to go home with is you, jay,”

jay looks at her with so much adoration in his eyes, she’s momentarily overwhelmed.

“wow,” she adds, “this horrid hangover is turning out so much better than i was expecting.”

all she receives is a wink from jay but it’s enough to keep her satisfied until they hit molly’s at the end of shift.

**Author's Note:**

> hahaha this was weirdly adorable and for some reason, took me forever to finish (i hate writing endings sometimes) 
> 
> loved writing will and jay.. will definitely do that again
> 
> also, i apologize is hailey seemed whiny or annoying.. idk what drunk hailey would be like so i just kinda went with the flow.. hope you guys liked it tho!!
> 
> also... i'm sort of feeling maybe a chapter two?? idk what do you guys think?
> 
> be sure to follow me on tumblr; ruzek-halstead!!


End file.
